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Safety Information

260908

Sigma-Aldrich

N-Bromophthalimide

95%

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About This Item

Empirical Formula (Hill Notation):
C8H4BrNO2
CAS Number:
2439-85-2
Molecular Weight:
226.03
Beilstein:
131211
EC Number:
219-467-9
MDL number:
MFCD00005888
UNSPSC Code:
12352100
PubChem Substance ID:
24855777
NACRES:
NA.22

Quality Level

100

Assay

95%

mp

194-198 °C (lit.)

functional group

imide

SMILES string

BrN1C(=O)c2ccccc2C1=O

InChI

1S/C8H4BrNO2/c9-10-7(11)5-3-1-2-4-6(5)8(10)12/h1-4H

InChI key

MARXMDRWROUXMD-UHFFFAOYSA-N

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Application

N-Bromophthalimide has been used:
  • as reagent in allylic amination reactions of alkenes
  • brominating reagent in enantioselective synthesis of multisubstituted biaryl derivatives by chiral phosphoric acid catalyzed asymmetric bromination
  • as a titrant in titrimetric determination of isoniazid in pure form or in tablets

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

260908-VAR:
260908-5G:
260908-25G:
260908-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK0193
STBJ4191
STBH3040
STBF4285V
STBD9654V

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A M el-Brashy et al.
Journal of pharmaceutical and biomedical analysis, 10(6), 421-426 (1992-06-01)
Two methods are proposed for the determination of isoniazid in pure form or in tablets. In the first method chlorpromazine hydrochloride, when treated with 2-iodoxybenzoic acid as an oxidant in 50% w/v o-phosphoric acid solution, is oxidized to chlorpromazine free
Titrimetric methods for the determination of some sulpha drugs using N-bromophthalimide and N-bromosaccharin.
K G Kumar et al.
The Analyst, 113(9), 1369-1372 (1988-09-01)
Tejas P Pathak et al.
Journal of the American Chemical Society, 134(14), 6120-6123 (2012-04-03)
We report the site-selective bromination of vancomycin to produce, with substantial efficiency, previously unknown monobromovancomycins, a dibromovancomycin, and a tribromovancomycin. We document the inherent reactivity of native vancomycin toward N-bromophthalimide. We then demonstrate significant rate acceleration and perturbation of the
Feng Chen et al.
Journal of the American Chemical Society, 135(4), 1232-1235 (2013-01-15)
A catalytic asymmetric bromocyclization of trisubstituted olefinic amides that uses a C(2)-symmetric mannitol-derived cyclic selenium catalyst and a stoichiometric amount of N-bromophthalimide is reported. The resulting enantioenriched pyrrolidine products, which contain two stereogenic centers, can undergo rearrangement to yield 2,3-disubstituted
Titrimetric determination of para-aminobenzoic acid using N-bromophthalimide and N-bromosaccharin.
K G Kumar et al.
Journal of pharmaceutical and biomedical analysis, 7(5), 627-631 (1989-01-01)
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